Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents
6 pages, 2 figures, 1 scheme, 2 tables.-- PMID: 12816498 [PubMed].-- Printed version published Jun 27, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0341113 A novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with steri...
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American Chemical Society
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ftcsic:oai:digital.csic.es:10261/20227 2024-02-11T09:57:25+01:00 Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents Abad, José Luis Soldevila, Carles Camps Díez, Francisco Clapés Saborit, Pere 2003-06-05 22195 bytes application/pdf http://hdl.handle.net/10261/20227 https://doi.org/10.1021/jo0341113 en eng American Chemical Society http://dx.doi.org/10.1021/jo0341113 Journal of Organic Chemistry 68(13): 5351-5356 (2003) 0022-3263 http://hdl.handle.net/10261/20227 doi:10.1021/jo0341113 1520-6904 none Chemoenzymatic methodology Secondary alcohols Enzymatic resolution Sex pheromone biosynthesis artículo http://purl.org/coar/resource_type/c_6501 2003 ftcsic https://doi.org/10.1021/jo0341113 2024-01-16T09:25:06Z 6 pages, 2 figures, 1 scheme, 2 tables.-- PMID: 12816498 [PubMed].-- Printed version published Jun 27, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0341113 A novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents is described. The key step is the kinetic lipase-catalyzed resolution of racemic mixtures of substituted propargylic alcohols. The efficiency of this new approach was tested in the preparation of the corresponding enantiomers of 1,11-hexadecandiol derivatives ((R)-5 and (S)-5). Two strategies were tested. In the first one, the racemic intermediate 1-octyn-3-ol (1) was resolved enzymatically and then elongated with 1-bromo-9,11-dioxadodecane. Alternatively, the racemic 1 can be elongated to the corresponding racemic 17,19-dioxa-7-eicosyn-6-ol (3) first and then resolved biocatalytically. Twelve commercially available lipases were screened for the kinetic resolution of these intermediates. Among them, Candida antarctica lipase (CAL-B) and Humicola lanuginosa lipase (HLL) were the best biocatalysts for the resolution of 1 (S enantiomer 90% ee, E = 35), and 3 (R enantiomer 90% ee, E = 34), respectively. CICYT and FEDER (AGL2001-0585) and Generalitat de Catalunya (2001SGR 00342). Peer reviewed Article in Journal/Newspaper Antarc* Antarctica Digital.CSIC (Spanish National Research Council) The Journal of Organic Chemistry 68 13 5351 5356 |
institution |
Open Polar |
collection |
Digital.CSIC (Spanish National Research Council) |
op_collection_id |
ftcsic |
language |
English |
topic |
Chemoenzymatic methodology Secondary alcohols Enzymatic resolution Sex pheromone biosynthesis |
spellingShingle |
Chemoenzymatic methodology Secondary alcohols Enzymatic resolution Sex pheromone biosynthesis Abad, José Luis Soldevila, Carles Camps Díez, Francisco Clapés Saborit, Pere Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents |
topic_facet |
Chemoenzymatic methodology Secondary alcohols Enzymatic resolution Sex pheromone biosynthesis |
description |
6 pages, 2 figures, 1 scheme, 2 tables.-- PMID: 12816498 [PubMed].-- Printed version published Jun 27, 2003.-- Supporting information available at: http://pubs.acs.org/doi/suppl/10.1021/jo0341113 A novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents is described. The key step is the kinetic lipase-catalyzed resolution of racemic mixtures of substituted propargylic alcohols. The efficiency of this new approach was tested in the preparation of the corresponding enantiomers of 1,11-hexadecandiol derivatives ((R)-5 and (S)-5). Two strategies were tested. In the first one, the racemic intermediate 1-octyn-3-ol (1) was resolved enzymatically and then elongated with 1-bromo-9,11-dioxadodecane. Alternatively, the racemic 1 can be elongated to the corresponding racemic 17,19-dioxa-7-eicosyn-6-ol (3) first and then resolved biocatalytically. Twelve commercially available lipases were screened for the kinetic resolution of these intermediates. Among them, Candida antarctica lipase (CAL-B) and Humicola lanuginosa lipase (HLL) were the best biocatalysts for the resolution of 1 (S enantiomer 90% ee, E = 35), and 3 (R enantiomer 90% ee, E = 34), respectively. CICYT and FEDER (AGL2001-0585) and Generalitat de Catalunya (2001SGR 00342). Peer reviewed |
format |
Article in Journal/Newspaper |
author |
Abad, José Luis Soldevila, Carles Camps Díez, Francisco Clapés Saborit, Pere |
author_facet |
Abad, José Luis Soldevila, Carles Camps Díez, Francisco Clapés Saborit, Pere |
author_sort |
Abad, José Luis |
title |
Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents |
title_short |
Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents |
title_full |
Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents |
title_fullStr |
Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents |
title_full_unstemmed |
Novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents |
title_sort |
novel chemoenzymatic strategy for the synthesis of enantiomerically pure secondary alcohols with sterically similar substituents |
publisher |
American Chemical Society |
publishDate |
2003 |
url |
http://hdl.handle.net/10261/20227 https://doi.org/10.1021/jo0341113 |
genre |
Antarc* Antarctica |
genre_facet |
Antarc* Antarctica |
op_relation |
http://dx.doi.org/10.1021/jo0341113 Journal of Organic Chemistry 68(13): 5351-5356 (2003) 0022-3263 http://hdl.handle.net/10261/20227 doi:10.1021/jo0341113 1520-6904 |
op_rights |
none |
op_doi |
https://doi.org/10.1021/jo0341113 |
container_title |
The Journal of Organic Chemistry |
container_volume |
68 |
container_issue |
13 |
container_start_page |
5351 |
op_container_end_page |
5356 |
_version_ |
1790609722660880384 |